17α-Ethynyl-3α-androstanediol

17α-Ethynyl-3α-androstanediol
Clinical data
Other names	HE3235; Apoptone; 17α-Ethynyl-5α-androstane-3α,17β-diol; 5α-Pregn-20-yne-3α,17α-diol
Identifiers
	IUPAC name (3R,5S,8R,9S,10S,13S,14S,17R)-17-ethynyl-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol;
CAS Number	183387-50-0;
PubChem CID	42611099;
ChemSpider	32698509;
UNII	891O182ZP5;
CompTox Dashboard (EPA)	DTXSID70171418 ;
Chemical and physical data
Formula	C21H32O2
Molar mass	316.485 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)O;
	InChI InChI=1S/C21H32O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,14-18,22-23H,5-13H2,2-3H3/t14-,15+,16+,17-,18-,19-,20-,21-/m0/s1; Key:CKAXZOYFIHQCBN-JRRMKBMNSA-N;

Ethynylandrostanediol (developmental code name HE-3235), or 17α-ethynyl-5α-androstane-3α,17β-diol, also known as Apoptone, is a synthetic, orally active, 17α-substituted analogue of the androstanediols which was under development for the treatment of prostate cancer and breast cancer but was discontinued.^[1]^[2]^[3] It has very low affinity for steroid receptors, including the ARTooltip androgen receptor, ERαTooltip estrogen receptor alpha, ERβTooltip estrogen receptor beta, PRTooltip progesterone receptor, and GRTooltip glucocorticoid receptor, and its mechanism of action is not well-characterized.^[1]^[4] It produces 5α-dihydroethisterone as an active metabolite, which may contribute importantly to its biological activity.^[1]

Ethandrostate, also known as 17α-ethynylandrost-5-ene-3β,17β-diol 3β-cyclohexanepropionate, is a related steroid.^[5]^[6]

References

^ ^a ^b ^c Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, Reading C, White S, Stickney D, Frincke J (2012). "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Invest New Drugs. 30 (1): 59–78. doi:10.1007/s10637-010-9517-0. PMID 20814732.
^ Trauger R, Corey E, Bell D, White S, Garsd A, Stickney D, Reading C, Frincke J (2009). "Inhibition of androstenediol-dependent LNCaP tumour growth by 17alpha-ethynyl-5alpha-androstane-3alpha, 17beta-diol (HE3235)". Br. J. Cancer. 100 (7): 1068–72. doi:10.1038/sj.bjc.6604987. PMC 2669987. PMID 19337256.
^ http://webcache.googleusercontent.com/search?q=cache:Jy1DYIHEUtQJ:adisinsight.springer.com/drugs/800025305
^ Koreckij TD, Trauger RJ, Montgomery RB, Pitts TE, Coleman I, Nguyen H, Reading CL, Nelson PS, Vessella RL, Corey E (2009). "HE3235 inhibits growth of castration-resistant prostate cancer". Neoplasia. 11 (11): 1216–25. doi:10.1593/neo.09960. PMC 2767223. PMID 19881957.
^ Ralph I. Dorfman (1962). Bioassay. Elsevier. pp. 224–228. ISBN 978-1-4832-7276-4.
^ Olson KB, Frawley TF, Stein AA, Shields D (1958). "Ethandrostate: endocrine effects and studies in treatment of cancer". Cancer. 11 (3): 537–45. doi:10.1002/1097-0142(195805/06)11:3<537::aid-cncr2820110313>3.0.co;2-w. PMID 13523561.

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